Toluene → N-Cbz-N-methyl-2-aminoethanol

Participants

Reaction Steps

To a stirred and cooled (0° C.) solution of N-methyl ethanolamine (3.10 g, 41.27 mmol), Et3 N (11.80 mL, 84.66 mmol) in DMF-H2O (3:1, v/v, 40 mL) was added dropwise 30% toluene solution of benzyl chloroformate (25.40 g, 49.13 mmol) for over 15 min. The resulting mixture was stirred for 1 day at room temp. The mixture was extracted with EtOAc. The extract was washed with sat. NaHCO3, brine, dried over Na2SO4, and evaporated. The residue was purified by column chromatography on silica-gel with n-hexane:EtOAc (3:1, v/v) then CHCl3 as eluent to give 4.67 g (54%) N-methyl-N-(benzyloxy carbonyl)ethanolamine as a colorless oil. 1H-NMR (CDCl3) d 1.82 (bs, 1 H), 3.00 (s, 3 H), 3.46 (bs, 2 H), 3.77 (bs, 2 H), 5.13 (s, 2 H), 7.29–7.36 (m, 5 H).

Provenance & Evidence